The more I think about it, I find freedom is a state of mind. Like Lydia said in a comment here, as long as what a person does feels authentic, a sense of freedom comes naturally. More than what a person actually does, it comes down to a person being authentic in the first place, to staying to true to one's self. I'd think if someone wants to do authentic things, then he'd have to be an authentic being first. (Side note, if you want to know more about authenticity, most of the existential philosophers wrote about it, like Kierkegaard, Heidegger, and Sartre.)
Our society's lack of accepting who we are and being totally cool with ourselves stands in the way of feeling free. We "need" plastic surgery to look better, we "need" to like the right music/movies/food/clothes, we "need" to constantly search for love, we "need" to be busy all the time ('cause if not, we're just lazy — not taking a break). But when it comes down to it, the things that hold us back from true freedom are just a bunch of hullabaloo.
(other photos via fashiongonerogue)